(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate

Base Information

• Chemical Name: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate
• CAS No.: 154520-16-8
• Molecular Formula: C₂₉H₄₈N₂O₄S
• Molecular Weight: 520.777
• Mol file: 154520-16-8.mol

Synonyms:(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate

Chemical Property of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate

There total 4 articles about (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate (188183-29-1) + methyl iodide (74-88-4) → (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate + (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate (154520-16-8)

Guidance literature:

With lithium diisopropyl amide; Yield given. Title compound not separated from byproducts; 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d;

DOI:10.1021/jo00088a034

Reference yield:

2-Cyano-3-methylbutanoic acid (22426-27-3) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate (154520-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1: PCl₅

2: 89 percent / AgCN / toluene / 4 h / 80 °C

3: 50 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

With silver cyanide; phosphorus pentachloride; lithium diisopropyl amide; In toluene;

DOI:10.1021/jo00088a034

Reference yield:

2-Cyano-3-methylbutanoyl chloride (98134-33-9) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2,3-dimethylbutanoate (154520-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / AgCN / toluene / 4 h / 80 °C

2: 50 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

With silver cyanide; lithium diisopropyl amide; In toluene;

DOI:10.1021/jo00088a034

upstream raw materials:

(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate

methyl iodide

isopropyl triflate

(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate

Downstream raw materials:

(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2,3-dimethylbutanoate